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Siesta Isles Real Estate Sold55+ Active AdultNo HOA

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Siesta Isles, 18435 Deep Passage Ln, Fort Myers Beach, Florida 33931, image 1
Sold - Mar 03, 2026
$900,000 $95K
  • 2 Beds
  • 2 Baths
  • 1,155 SqFt
  • $779/SqFt
House sold in Siesta Isles
18435 Deep Passage Ln, Fort Myers Beach, FL 33931
Welcome to siesta isles, one of the best waterfront communities in ft. Myers and swfl! Don't let an opportunity like this pass you by! This remarkable cottage like home, located on a direct sailboat access canal, is as quaint of an oasis you'll find anywhere. This beautiful gem offers stunning views, looking down a wide, deep canal with quick , direct access to the gulf. Home is immaculately maintained and is ideal for the boater enthusiast. The metal roof, colorful exterior, plush landscaping, combined with the lagoon style pool and spa makes living in paradise a reality. Home features many upgrades, a reinforced newer seawall (2019), newer roof (2022), 13000 lb. Boat lift, fencing (2022), and ac units (2022). This community is conveniently located to fine waterfront restaurants, shopping and the beautiful sandy beaches of sanibel and ft. Myers beach. Schedule an appoitment today , you will not be disappointed.
Siesta Isles, 18404 Cutlass Dr, Fort Myers Beach, Florida 33931, image 1
Sold - Mar 02, 2026
$1,114,000 $100K
  • 5 Beds
  • 3 Baths
  • 2,258 SqFt
  • $493/SqFt
House sold in Siesta Isles
18404 Cutlass Dr, Fort Myers Beach, FL 33931
Luxury waterfront estate in fort myers beach welcomes you to the pinnacle of coastal living! Your dream home awaits at this luxurious waterfront estate in the enchanting fort myers beach! Set in the coveted enclave of siesta isles, this remarkable property offers an unparalleled opportunity to immerse yourself in a world where opulence meets the tranquil charm of canal-side living. With breathtaking views, sophisticated finishes, and an enviable location, this estate is the epitome of a perfect coastal retreat that will captivate the most discerning homeowners. The thoughtfully designed floor plan features floor-to-ceiling windows that invite an abundance of natural light while framing unobstructed views of the picturesque waterfront, a canvas of serene beauty that brings nature indoors. The heart of the home is the great room, an elegant space perfect for entertaining or unwinding in a peaceful environment. Every detail of this home has been meticulously crafted to offer modern luxury while maintaining the timeless charm that defines waterfront living. For the culinary enthusiast, the gourmet kitchen is a dream come true. Equipped with high-end stainless steel appliances, classic cabinetry, and a soothing organic palette, this kitchen is designed to inspire creativity. Step outside, and the luxurious lifestyle continues to flourish in your private outdoor oasis. The outdoor area is an entertainer's paradise, featuring a stunning heated swimming pool and spa, surrounded by towering palms. For the water enthusiasts, this estate truly shines with its very own private dock positioned on a spacious deep-water access canal. This exceptional feature accommodates large boats, offering seamless access to the aquatic adventures that southwest florida has to offer. Just minutes away from the pristine shores of fort myers beach by car or boat, you'll have quick access to some of the most stunning white-sandy beaches and vibrant coastal communities, including the iconic sanibel and captiva islands. The neighborhood is rich with local eateries, lively pubs, and diverse entertainment options, ensuring that fun and excitement are always just around the corner. Nestled on a cul-de-sac just steps from the bay, this estate positions you perfectly to take advantage of all the aquatic adventures the region has to offer. Whether you're an avid boater or simply appreciate the beauty of waterfront living, this property promises an enviable lifestyle for those who cherish the ocean. This luxurious waterfront estate is not just a house; it's a lifestyle choice that embodies the essence of coastal living. With stunning architecture, high-end finishes, and an unbeatable location, this property is a sanctuary where you can relax, rejuvenate, and bask in nature's beauty every day. Own your dream home in one of florida's most sought-after locales and revel in the magic of everyday living.
Siesta Isles, 18468 Cutlass Dr, Fort Myers Beach, Florida 33931, image 1
Sold - Feb 27, 2026
$1,700,000 $150K
  • 5 Beds
  • 4 Baths
  • 3,114 SqFt
  • $546/SqFt
House sold in Siesta Isles
18468 Cutlass Dr, Fort Myers Beach, FL 33931
Cannot beat the location, price, boat lift and dock and home! A true boater’s paradise – with unmatched hurricane water surge protection! Minutes from fort myers beach and sanibel island, this stunning waterfront home sits in siesta isles—voted one of southwest florida’s premier boating communities. Enjoy deep-water, sailboat gulf access with no miserable mile, surrounded by multi-million-dollar estates that define luxury coastal living. A first in sw florida we’ve just invested over $50, 000 in custom-engineered flood barriers—40" high, precision-fit for every door and window, including the massive 23' x 12'-- 90° sliders in the lanai. Designed to protect against storm surge, these barriers offer peace of mind and unparalleled property protection. Waterfront perfection! • 101 ft. Of shoreline with a new 14, 000-lb boat lift & canopy (fits 28–30 ft. Boats) • composite dock with water & electric hookups • seawall space for additional watercraft upgrades & construction quality! • new flat tile roof—glued, screwed, with new sheathing & underlayment • 3, 114 sq. Ft. Under air, designer ceramic wood-look plank flooring • 16-ft. Ceilings in gathering room with 10-ft. Pocket 90° sliders + custom electric shades chef’s dream kitchen! Three rows of modern white cabinetry, oversized quartz waterfall island, hidden walk-in pantry, double oven, and premium finishes—perfect for both casual meals and elegant entertaining. Flexible luxury living! • 5 bedrooms / 4 full baths • 3 ensuite bedrooms (including an upstairs second master with private entry & laundry hook-up) outdoor oasis! Resort-style pool with spa & lap area, high-end outdoor kitchen with bar & sink, paver driveway & walkways, lush night-lit landscaping—all overlooking breathtaking coastal views where dolphins and manatees often visit. Siesta isles homes rarely offer this level of luxury, boating access and storm protection!—schedule your private showing today!
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Siesta Isles, 18276 Cutlass Dr, Fort Myers Beach, Florida 33931, image 1
Sold - Nov 21, 2025
$2,850,000 $650K
  • 6 Beds
  • 61/2 Baths
  • 5,767 SqFt
  • $494/SqFt
House sold in Siesta Isles
18276 Cutlass Dr, Fort Myers Beach, FL 33931
Waterfront living at its best! Welcome to your ultimate fun-filled getaway just minutes from fort myers beach! This 6-bedroom, 7-bathroom canal-front home is designed for making unforgettable memories—whether you're cruising the waterways, hosting poolside parties, or soaking up sun-filled days with the people you love most. The ground level sets the vibe with a custom wrap-around bar—complete with a 12’ shark hanging overhead! Kick back in the theater room or perfect your swing on the indoor golf simulator. The relaxed lounge area flows seamlessly to your private saltwater pool and spa. A tiki hut adds a tropical touch, while the massive sun deck with dining and lounge areas—features a boat lift and large slip for your water toys, so you’re always just moments from your next adventure. The 80' wide canal makes it easy to accommodate most vessels. Take the private elevator up to the second floor, where everyday living meets effortless entertaining. The open-concept layout includes a gourmet kitchen with built-in appliances, a center island cooktop, an oversized breakfast bar, and a spacious eat-in dining area. Exposed beams, a stone accent wall, and a cozy fireplace add warmth and style. Slide open the collapsible glass doors and expand your living space onto a huge balcony overlooking the pool and canal. With a full outdoor kitchen and built-in bbq, it’s the perfect place to grill, gather, and enjoy the coastal breeze. Upstairs, the third floor features three additional bedrooms—including two spacious en-suite rooms and a luxurious primary suite with a spa-like bathroom offering a soaking jet tub and an expansive walk-around shower. But the real showstopper? The private, oversized third-floor balcony, where you’ll enjoy epic panoramic views of the canal, nature preserve, and front-row seats to southwest florida’s jaw-dropping sunsets—a picture-perfect backdrop for peaceful mornings or starlit evenings. Conveniently tucked away from the tourist buzz yet just a short ride to fort myers beach, sanibel island, and cayo costa state park, this home delivers the perfect blend of adventure, comfort, and coastal lifestyle. From boat days and bbq nights to movie marathons and poolside laughs—this is where lifelong memories are made! **be sure to request the cinematic video tour and 3d walk-through!
Siesta Isles, 18548 Cutlass Dr, Fort Myers Beach, Florida 33931, image 1
Sold - Oct 14, 2025
$1,200,000 $350K
  • 5 Beds
  • 4 Baths
  • 2,172 SqFt
  • $552/SqFt
House sold in Siesta Isles
18548 Cutlass Dr, Fort Myers Beach, FL 33931
Discover your dream waterfront estate, your ultimate slice of paradise in the heart of fort myers beach! Nestled within the serene enclave of siesta isles, this stunning property offers a unique opportunity to experience the harmonious blend of opulence and tranquil canal-side living. With breathtaking views, high-end finishes, and an ideal locale, it is a dream come true for those seeking the perfect coastal retreat. As you step through the grand entrance, you'll immediately be captivated by the expansive, bright, and airy spaces that define this majestic estate. The cleverly designed floor plan features floor-to-ceiling windows that flood the interiors with natural light while providing unobstructed views of the picturesque waterfront inviting the beauty of nature indoors. The great room serves as the heart of the home, where you can entertain or simply unwind while soaking in the calming sights of the serene blue waters just beyond. Every inch of this home has been meticulously remodeled to offer modern luxury while maintaining its timeless charm. Equipped with brand new high-end stainless steel appliances and quartz counters, the gourmet kitchen is a culinary enthusiast's dream. Whether you're preparing a casual breakfast or hosting a lavish dinner party, this kitchen seamlessly integrates with the open concept living area, ensuring that you'll never miss a moment with your guests. Stepping outside, the luxurious lifestyle continues. The outdoor area is an entertainer's paradise, featuring a private heated swimming pool and spa surrounded by swaying majestic palms. For the water enthusiasts, the property comes complete with its very own private dock situated on a spacious deep-water access canal. This exceptional feature accommodates large boats, making it easy to embrace the aquatic adventures southwest florida has to offer. The location of this magnificent estate is unparalleled. Situated just minutes away from fort myers beach by car or boat, you'll have easy access to some of the most stunning white sandy beaches and vibrant coastal communities, including sanibel and captiva islands. The neighborhood is brimming with local eateries, lively pubs, and a variety of entertainment options, ensuring that you're always close to fun and excitement. There is no hoa, allowing you the freedom to enjoy your property to the fullest without any restrictions. Siesta isles is recognized as one of the premier deep-water boating communities in southwest florida, offering quick access to the gulf of mexico. You're merely the third lot off the bay, positioning you perfectly to take advantage of all the aquatic adventures the region has to offer. Experience the magic of this tropical oasis where luxury meets tranquility and every day feels like a vacation.
Siesta Isles, 18308 Cutlass Dr, Fort Myers Beach, Florida 33931, image 1
Sold - Aug 29, 2025
$730,000 $135K
  • 3 Beds
  • 3 Baths
  • 2,122 SqFt
  • $344/SqFt
House sold in Siesta Isles
18308 Cutlass Dr, Fort Myers Beach, FL 33931
Discover your dream waterfront home in fort myers beach! Seize the opportunity to finish building your dream waterfront home in the exclusive siesta isles community of fort myers beach, where luxury meets coastal living. This extraordinary property is perfectly situated to cater to boating enthusiasts and families alike, nestled in one of the best boating communities in the area, offering direct sailboat access to the open waters. Experience the thrill of customizing your home to reflect your personal taste and style. The possibilities are endless, allowing you to design a space that meets your every desire. Whether you envision an expansive open-concept living area, a gourmet kitchen, or serene bedrooms with sweeping water views, the canvas is yours to create. Step outside to discover an outdoor oasis designed for entertaining. The covered patio invites you to relax in the shade or host vibrant gatherings, while the private swimming pool offers a cool retreat on warm sunny days. Imagine making unforgettable memories as you bask in the sun or enjoy a tranquil evening by the water. For those who cherish life on the water, this property features a private slip spacious deep-water access canal, capable of accommodating large boats. Embrace the boating lifestyle and set sail into the sparkling waters of southwest florida, where adventure awaits at every turn. Indulge in fishing, water sports, or leisurely boat rides as you explore the stunning coastal landscapes of the gulf of mexico. This idyllic setting promises a peaceful retreat from the hustle and bustle of everyday life, allowing you to unwind and rejuvenate in the comfort of your own home. Just minutes away from fort myers beach, you'll have convenient access to pristine white sandy beaches and vibrant coastal communities, including the renowned sanibel and captiva islands. One of the standout features of this property is that there is no homeowners association (hoa), granting you the freedom to enjoy your property without restrictions. Whether you're an avid boater or simply appreciate the beauty and serenity of waterfront living, this estate offers the ultimate lifestyle for those who cherish the ocean. With the option to build out your custom home, this is not just a property; it is an invitation to a life of luxury and leisure. Option available to complete your paradise dream home with the seller. Begin a new chapter in your life and embrace all the beauty and adventure that come with this exceptional waterfront estate in fort myers beach!
Siesta Isles, 18307 Cutlass Dr, Fort Myers Beach, Florida 33931, image 1
Sold - Jul 31, 2025
$820,000 $155K
  • 3 Beds
  • 3 Baths
  • 2,452 SqFt
  • $334/SqFt
House sold in Siesta Isles
18307 Cutlass Dr, Fort Myers Beach, FL 33931
Design your dream waterfront escape in fort myers beach! Imagine waking up every day in a stunning waterfront home that you designed just the way you wanted. Nestled in the highly sought-after siesta isles community, this luxury property is an incredible opportunity for you to finish building your dream home in one of the most prestigious boating communities in southwest florida. With direct sailboat access, you'll be just moments away from endless aquatic adventures, making every day feel like a vacation. As you step onto the property, you'll instantly be captivated by the open concept floor plan and floor to ceiling windowscapes. The outdoor entertainment area is designed to create unforgettable memories. A covered patio beckons you to relax in the shade while enjoying the gentle breeze, and the private swimming pool sparkles invitingly under the warm florida sun. This is the perfect setting for hosting gatherings, or simply unwinding after a long day. Water enthusiasts will revel in the property's exceptional feature, a spacious private dock situated on a sprawling deep-water access canal. This prime docking space accommodates large boats with ease, providing you the freedom to explore the stunning waters of southwest florida at your leisure. Location is everything, and this magnificent estate offers unparalleled access to both the serenity of nature and the vibrancy of local culture. Just minutes away from fort myers beach by car or boat, you'll find yourself immersed in some of the most stunning white sandy beaches in the world. Explore nearby sanibel and captiva islands, where you can indulge in local cuisine, enjoy water sports, or simply bask in the sun. This property is the absence of an hoa, allowing you to have complete freedom over your home without any restrictions. Siesta isles is celebrated as one of the premier deep-water boating communities in the region, facilitating quick access to the gulf of mexico. This waterfront estate in fort myers beach is not just a house; it's a lifestyle choice that encapsulates the very essence of coastal living. With plumbing and framing nearly complete, the canvas is yours to finish according to your desires. Whether you envision a modern paradise or a charming coastal retreat, the options are endless. Don't miss out on this incredible opportunity to make your paradise dream home come true. With the option to build out your custom home with the seller's assistance, your waterfront oasis in one of florida's most coveted locales is within reach. Seize the moment, start crafting the life you've always desired in the heart of southwest florida! Brand new steel roof & brand new pool cage 2025!
Siesta Isles, 18467 Deep Passage Ln, Fort Myers Beach, Florida 33931, image 1
Sold - Mar 24, 2025
$1,400,000
  • 4 Beds
  • 3 Baths
  • 2,300 SqFt
  • $609/SqFt
House sold in Siesta Isles
18467 Deep Passage Ln, Fort Myers Beach, FL 33931
Attention boaters, this 4/3/3 estate home sits in the prestigious deep water, sailboat access community of siesta isles with no bridges & direct access to the gulf of mexico just 1 mile from fort myers beach. The home boasts an incredible back yard with a resort style pool area ideal for entertaining guests & picture-perfect views of the water basin. This beautifully updated home offers unparalleled direct access to the gulf of mexico, mantanzas pass, or the beach & islands—all within a mere 10 minutes from your brand new oversize trex dock with two boat lifts (one covered 13, 000 pound /the other set up for 10, 000 pounds )with the seawall/ canal capacity to accommodate up to a 50’ vessel. Spanning nearly 2300 sq ft of insurable, livable square footage, this residence presents a seamless blend of luxury and comfort. The kitchen, opens to the family room and dining area, creates an inviting atmosphere perfect for entertaining or relaxing with loved ones. Step onto the large fully glass, screened balcony and enjoy panoramic views of the pool, canal and basin… ideal spot for morning coffee or evening cocktails. Unwind in the spacious master bedroom featuring a walk-in closet, custom walk-in shower & separate soaker. The fully finished downstairs offers endless possibilities, whether for entertaining guests, in-law suite, or a kids haven. Plus, discover a versatile flex room perfect for a 3rd garage, fitness area or workshop, catering to your lifestyle needs. Step into outdoor living at its finest on the expansive natural travertine patio, complete with an outdoor kitchen featuring built-in gas grills, kitchen sink, in-counter coolers and set up for outdoor undercounter fridges among other amenities. This home underwent an extensive renovation. Every aspect of this property has been carefully remodeled, featuring numerous enhancements, such as elegant wood floors throughout, level 5 granite countertops, custom bathrooms, elegant chefs kitchen, a wet bar, all-new appliances, whole home water treatment & 2 laundry & recently installed a/c systems. Additionally, all windows and doors are full impact rated with electric sun shutters for added convenience and privacy & a long lasting, beautiful standing seam metal roof. Unlike most homes on the water, this home is pre-firm meaning the downstairs is insurable, making it stand apart from the rest! This house has been immaculately well kept, with too many updates to list here but receipts are available to the seriously interested. Schedule your private showing today to experience the ultimate florida lifestyle and let your waterfront dreams come true!
Siesta Isles, 18276 Deep Passage Ln, Fort Myers Beach, Florida 33931, image 1
Sold - Mar 18, 2025
$2,075,000
  • 4 Beds
  • 42/2 Baths
  • 4,318 SqFt
  • $481/SqFt
House sold in Siesta Isles
18276 Deep Passage Ln, Fort Myers Beach, FL 33931
The dream of living in sw florida can be a reality! This spectacular home with stunning sunsets exudes quality craftsmanship inside & out! Four ensuite bedrooms & baths makes this home perfect for family & guests to have their own private space. The gourmet kitchen was designed with entertaining in mind! Large central island, thermador appliances, wine cooler, granite/quartz countertops, walk in pantry, many drawers and cabinets. Dual sinks allow separation of food prep & clean up. The entire ground floor can be used as a master suite or guest suite containing a mini-kitchen, washer/dryer and lounge area which opens directly to the pool! Impact doors, insulated windows & doors throughout lends a bright airy feel to living spaces. Plenty of outdoor living with multiple decks, outdoor fire pit, swimming pool and top of the line boat dock. The gulf, sanibel island and sw florida beaches are only one mile away! Amazing investment opportunity! Weekly rentals allowed. Owners have taken impeccable care of this dynamic coastal home!
Siesta Isles, 18443 Deep Passage Ln, Fort Myers Beach, Florida 33931, image 1
Pending
$1,675,000
  • 5 Beds
  • 3 Baths
  • 3,170 SqFt
  • $528/SqFt
House for sale in Siesta Isles
18443 Deep Passage Ln, Fort Myers Beach, FL 33931
Welcome to siesta isles, one of the best waterfront communities in ft. Myers beach and swfl! This immaculate home offers stunning views, looking down the deepest, quickest , sailboat, gulf access canal in the area. This beautiful 5 bedroom, 3 full bath home, with oversized 2 car garage offers 3170 sq. Ft of ac living space. The upstairs interior has a great room floor plan designed for entertaining, and a kitchen fit for a chef. Quartz countertops , glass tile backsplash, and exqusite ss ge monogram appliances, including counter depth french door fridge/freezer, french door oven, warming drawer, and a advantium convection/microwave. An expansive quartz center island is equipped with an induction cooktop and large prep sink. Additionally there is a beverage station/breakfast bar with wine cooler and dishwasher. The entire house has newer impact windows/doors and brand new exterior flood barriers on all first floor openings. The first floor level has all been redone, remediated and offers two spacious bedrooms, decorative full size bathroom, including washer and dryer, and family room for additional entertainment enjoyment. For the full florida lifestyle the exterior offers a heated salt water pool and spa, with decorative travertine tile decking. Top off the outside with your own 10, 000 lb lift with framed cover, composite walkway and decking for the enthusiastic boater and fisherman.The seawall, metal roof and hardboard siding were all completed in 2020. All furnishings can be included for a turn -key purchase.
Siesta Isles, 18547 Cutlass Dr, Fort Myers Beach, Florida 33931, image 1
Sold -
$695,000
  • 0.27 Acres
  • $2,574,074/Acre
Land sold in Siesta Isles
18547 Cutlass Dr, Fort Myers Beach, FL 33931
Build your waterfront paradise in fort myers beach! This unique opportunity in the prestigious siesta isles community of fort myers beach invites you to customize your dream residence just the way you envision it. Picture waking up every morning to breathtaking views, the gentle sound of water lapping at your private dock, and the exhilaration of living in one of southwest florida's best boating communities all just three lots from the bay! This exceptional property offers more than just prime real estate; it provides a lifestyle of leisure, adventure, and unparalleled beauty. With direct sailboat access and a spacious deep-water access canal right at your doorstep, you'll have the freedom to embark on aquatic adventures whenever you desire. Your very own private dock is perfect for accommodating large boats, empowering you to explore the stunning waters of the gulf of mexico with ease. As the sun sets, imagine soaking in the vibrant hues that dance across the sky, reflected on the glistening waters of your backyard. This picturesque scene serves as a daily reminder of the tranquil lifestyle that waterfront living affords. The sunsets here are nothing short of magical, creating an idyllic backdrop for your everyday life and providing the perfect setting for gatherings. Location is key, and this magnificent estate boasts an enviable position just minutes away from the stunning white sandy beaches of fort myers beach. Whether you prefer to travel by car or boat, you will have quick access to the sun-kissed shores and vibrant coastal communities of sanibel and captiva islands. Take advantage of the freedom that comes with owning a property in this area there is no homeowners association (hoa) to impose restrictions on your enjoyment. This means you can truly make this space your own, designing your dream home without limitations. This waterfront property isn't just about luxury; it's about embracing a lifestyle that celebrates the essence of life by the water. Imagine evenings spent entertaining friends on your deck, mornings sipping coffee as dolphins play in the canal, and weekends exploring the diverse marine life that thrives just beyond your back door. The memories you'll create in this home will be cherished for a lifetime. You have the option to work with the seller to build out your custom dream home. Make your paradise dream home come true in siesta isles, where stunning views, luxurious living, and the coastal lifestyle you desire await you!
Siesta Isles, 18195 Cutlass Dr, Fort Myers Beach, Florida 33931, image 1
Pending
$1,125,000 $225K
  • 4 Beds
  • 3 Baths
  • 2,534 SqFt
  • $444/SqFt
House for sale in Siesta Isles
18195 Cutlass Dr, Fort Myers Beach, FL 33931
Price, price, priced to sell now!A boater's dream! This 4 bedroom, 3 bathroom waterfront pool home with over 2500 square feet under air is located in the sought-after siesta isles neighborhood. The interior of the home has been remodeled to perfection with high end finishings throughout, inclusive of porcelain wood plank tile, built in bar with wine refrigerator, custom tiled bathrooms, modern lighting and so much more. The chef's kitchen with soft close white shaker cabinetry, gorgeous quartz waterfall counters, and a huge island overlooks the main living and dining areas, great for entertaining! Step outside and relax in your pool or hot tub while watching the dolphins and manatee. With 75 feet on this deep waterway, your boating and sailing options are endless from your private dock just minutes from the gulf. Nearly everything is new and has been fully permitted! Being sold turnkey furnished with no rental restrictions, this home is perfect for a snowbird, your new full-time residence, investment, or a combination thereof. Seller financing and/or lease options available.
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Car-Dependent. Almost all errands require a car.
11

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Minimal Transit. It is possible to get on a bus.
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Somewhat Bikeable. Minimal bike infrastructure.
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Bearable noise.
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